EP4076362A1 - Formulations offrant une performance parfumée de longue durée - Google Patents

Formulations offrant une performance parfumée de longue durée

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Publication number
EP4076362A1
EP4076362A1 EP21710183.1A EP21710183A EP4076362A1 EP 4076362 A1 EP4076362 A1 EP 4076362A1 EP 21710183 A EP21710183 A EP 21710183A EP 4076362 A1 EP4076362 A1 EP 4076362A1
Authority
EP
European Patent Office
Prior art keywords
long
fragrance composition
lasting fragrance
composition
lasting
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21710183.1A
Other languages
German (de)
English (en)
Inventor
Vera Tchakalova
Addi Fadel
Aude DAUGERON-JOUAULT
Laura MESMIN
Madelyne PHAM
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
Original Assignee
Firmenich SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of EP4076362A1 publication Critical patent/EP4076362A1/fr
Pending legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2101/00—Chemical composition of materials used in disinfecting, sterilising or deodorising
    • A61L2101/32—Organic compounds
    • A61L2101/44—Heterocyclic compounds

Definitions

  • the present invention relates to compositions and methods for providing long- lasting fragrance performance.
  • Maintaining fragrance intensity and/or profile over time is an important consideration for a commercial fragrance composition.
  • perfumery industry there is a constant need to find new ways to prolong the intensity and perception of perfumes over time.
  • a fragrance composition should maintain intensity and/or fragrance profile for at least 8 hours to satisfy consumer need.
  • fragrance composition which retains a significant portion of its initial fragrance character over time. It is also desirable that the fragrance strength of the fragrance composition remains noticeable to the consumer over long periods of time.
  • Formulations according to the present invention impart to consumers long-lasting perception and/or intensity of a perfume during fragrance wear with acceptable skin feel.
  • the present invention provides long-lasting fragrance compositions, methods, and uses for prolonging the performance of a fragrance oil.
  • a long-lasting fragrance composition according to the present invention comprises oil, a gelator, wherein the gelator is 0.01 to 15% w/w of the long-lasting fragrance composition; a volatile solvent; and water.
  • the gelator is 0.3 to 0.6% w/w of the long-lasting fragrance composition.
  • a gelator of the present invention may be selected from the group consisting of: an n-alkane having a greater than 16 CH 2 chain, a hydroxyalkanoic acid, hydroxy-octadecanoyl, hydroxy-hexadecanoyl, a dihydroxyalkanoic acid, a dicarboxylic acid, a fatty acids alkyl ester with an alkyl chain length greater than 20 CH 2 groups, a hydroxyalkanoic alcohol, a glycyrrhizic acid, an anthryl derivatives, dendrimers n-alkanes, oligo(p-phenylenevinylene), dipyridylurea-carboxylic acid combination, diamine linked Dendron, dibutyl ethylhexanoyl glutamide, dibutyl lauroyl monoglycerol, dibutyl lauroyl 2-glycerol, dibutyl lauroyl glycerate, dibutyl la
  • the long-lasting fragrance composition includes a fragrance oil, a gelator and an amphiphilic oil-soluble compound.
  • the amphiphilic oil- soluble compound may be 0.01% to 40% w/w of the long-lasting fragrance composition. In other aspects, the amphiphilic oil-soluble compound is 0.5% to 30% w/w of the long-lasting fragrance composition.
  • amphiphilic oil-soluble compound of the present invention includes a compound having one of the following chemical structures: or where n represents the number of CH2 groups and is greater than 14 and m represents the number of unsaturated C-C bounds and is greater than or equal to 1, and Ri is selected from the group consisting of:
  • serinolamide methylpropanediolamide, ethylpropanediolamide, urea, a urea alcohol, biuret, a biuret alcohol, anandamine, glycerol ether, a glycolipid, and a combination thereof.
  • amphiphilic oil-soluble compound is glycerol monooleate or phytantriol or combination thereof.
  • a long-lasting fragrance composition of the present invention may comprise 0.01% to 40% w/w of an amphiphilic oil-soluble compound, a volatile solvent, and water.
  • the amphiphilic oil-soluble compound may be 0.5 to 10% w/w of the long-lasting fragrance composition.
  • a fragrance oil may comprise from 0.01 to 70% w/w of the long-lasting fragrance composition.
  • a long-lasting fragrance composition according to the present invention may comprise a fragrance oil, 0.01% to 40% w/w of the long-lasting fragrance composition of an amphiphilic oil-soluble compound, a volatile solvent, and water.
  • the amphiphilic oil-soluble compound is 0.5 to 10% w/w of the long-lasting fragrance composition.
  • the water is 0.01 to 60% w/w of the long-lasting fragrance composition. In other aspects, the water is 0.7% - 60% w/w of the long-lasting fragrance composition. In aspects of the invention, the water content may be 0.1 to 60 % w/w of the long-lasting fragrance composition; 0.7 to 50 % w/w of the long-lasting fragrance composition; or 1% to 30% w/w of the long-lasting fragrance composition.
  • the volatile solvent may be, for example, ethanol, isopropyl alcohol, an ether, or mixtures thereof.
  • a long-lasting fragrance composition of the present invention may further include a modulator.
  • the modulator may be selected from the group consisting of: methyl glucoside polyol; ethyl glucoside polyol; propyl glucoside polyol; isocetyl alcohol; PPG-3 myristyl ether; neopentyl glycol diethylhexanoate; sucrose laurate; sucrose dilaurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose distearate, sucrose tristearate, hyaluronic acid disaccharide sodium salt, sodium hyaluronate, propylene glycol propyl ether; dicetyl ether; polyglycerin-4 ethers; isoceteth-5; isoceteth-7, isoceteth-10; isoceteth-12; isoceteth-15; isoceteth-20; isoceteth-25; is
  • the modulator comprises 0.5% to 20% w/w of the total weight of the long-lasting fragrance composition. In an aspect of the present invention, the modulator comprises 1% w/w of the total weight of the long-lasting fragrance composition. In a further aspect, the modulator comprises 2% w/w of the total weight of the long-lasting fragrance composition. In another aspect, the modulator comprises 3% w/w of the total weight of the long-lasting fragrance composition. In further aspects, the modulator may comprise 4% or 5% w/w of the total weight of the long-lasting fragrance composition.
  • amphiphilic oil-soluble compound has one of the following chemical structures: where n represents the number of CH2 groups and is greater than 14 and m represents the number of unsaturated C-C bounds and is greater than or equal to 1, and Ri is selected from the group consisting of:
  • amphiphilic oil-soluble compound is glycerol monooleate or phytantriol or a combination thereof. In some embodiments, the amphiphilic oil-soluble compound comprises from 1% to 5% w/w of the total weight of the long-lasting fragrance composition. In another embodiment, the amphiphilic oil-soluble compound comprises about 3% of the total weight of the long-lasting fragrance composition.
  • 40 to 100% of the fragrance oil in the long-lasting fragrance composition is a volatility component comprising at least one perfume raw material having a vapor pressure greater than 0.0008 Torr at 22°C.
  • the volatility component comprises at least one perfume raw material having a vapor pressure greater than 0.08 torr.
  • the long-lasting fragrance composition may further comprise a second perfume raw material having a vapor pressure greater than 0.08 Torr at 22°C.
  • 0.08 to 85% of the fragrance oil in the long-lasting fragrance composition is a volatility component comprising at least one perfume raw material having a vapor pressure in the range of 0.0008 to 0.08 Torr at 22°C.
  • the long-lasting fragrance composition may further comprise a second perfume raw material having a vapor pressure in the range of 0.0008 to 0.08 Torr at 22°C.
  • the present invention encompasses a leave-on volatile solvent-containing consumer product comprising a long-lasting fragrance composition.
  • the leave-on volatile solvent containing consumer product may be Cosmetic, Eau de Toilette, Eau de perfume, Eau de Cologne, Body mist, body spray, Body splash, Hair mist, air care spray, Hair Leave products, Fabric refreshers, and Deodorant.
  • the leave-on volatile solvent containing consumer product may further comprise a dye, a UV filters, an antioxidant, a quencher, a chelating agent, a solubilizer, a moisturizer, a humectant, an anti-aging active, a soothing agent, emollients, an anti-pollution active, or a combination thereof.
  • Figure 1 is a bar graph showing the relative intensity of fragrance ingredient styrallyl acetate, solubilized in the formulations EDT 1-4 in the head space at different moments of evaporation.
  • Figure 2 is a bar graph showing the relative intensity of fragrance A ingredients after 6h of evaporation from formulations EDT2 (with gelator AGA)
  • Figure 3 is a bar graph showing the effect of compound concentration on fragrance retention after 6 hours evaporation at 32°C.
  • Figure 4 is a bar graph showing results from a sensory panel comparison of
  • FIG. 5 is a bar graph showing the results from a sensory panel comparison using a mixture of GMO and Hedione. Sensory panels compared Fragrance SP in EDT without and with 3% GMO; Fragrance SP in EDT without and with 5% Hedione; and Fragrance SP in EDT without and with 3% GMO + 5% Hedione.
  • Figure 6 a and b are bar graphs showing the performance of two highly volatile fragrance ingredients, benzyl acetate and dihydromyrcenol, after evaporation at 2, 4 and 6 hours and compared it to the performance of the reference sample EDTO (value 1).
  • the intensity of the fragranced ingredients after 6 hours of evaporation was significantly higher in the presence of phytantriol and the mixture of phytantriol and gelator.
  • Figure 7 a and b are bar graphs showing the intensity of (A) benzyl acetate with 10% phytantriol, and benzyl acetate with 10% phytantriol and b-cyclodextrin (CD); and (B) dihydromyrcenol with 10% phytantriol, and dihydromyrcenol with 10% phytantriol and b- cyclodextrin.
  • Figure 8 is a graph showing the total area sums throughout evaporation of 5% Phytantriol 2% Polymethylol and 0.3% EB21 with Research Accord HT1 formula vs. RAHT1 formula alone. The data shows a higher retention of the sum of all compounds with 5% Phytantriol 2% Polymethylol and 0.3% EB21 throughout the entire evaporation against the control.
  • Figure 9 is a graph showing total area sums throughout evaporation of 5% Phytantriol 2% Schercemol and 0.3% EB21 with Research Accord HT1 formula vs. RAHT1 formula alone. The data shows a higher retention of the sum of all compounds with 5% Phytantriol 2% Schercemol and 0.3% EB21 throughout the entire evaporation against the control.
  • Figure 10 is a graph showing direct injection data at 1 hour evaporation of 5% Phytantriol 2% Polymethylol and 0.3% EB21 with Research accord HT1 formula vs. HT1 formula alone. The data shows a higher retention of all compounds and most noticeably high and mid volatility notes on the left.
  • Figure 11 is a graph showing direct Injection data at 1 hour evaporation of 5% Phytantriol 2% Schercemol and 0.3% EB21 with Research accord HT1 formula vs. HT1 formula alone. The data shows a higher retention of all compounds and most noticeably high and mid volatility notes on the left.
  • Figure 12 is a graph showing direct Injection data at 2 hours evaporation of 5% Phytantriol 2% Polymethylol and 0.3% EB21 with Research accord HT1 formula vs. HT1 formula alone. The data shows a higher retention of all compounds and most noticeably high and mid volatility notes on the left.
  • Figure 13 is a graph showing direct Injection data at 2 hours evaporation of 5% Phytantriol 2% Schercemol and 0.3% EB21 with Research accord HT1 formula vs. HT1 formula alone. The data shows a higher retention of all compounds and most noticeably high and mid volatility notes on the left.
  • Figure 14 is a graph showing direct Injection data at 4 hours evaporation of 5%
  • FIG. 17 is a graph showing direct injection data at 6 hours evaporation of 5% Phytantriol 2% Schercemol and 0.3% EB21 with Research accord HT1 formula vs. HT1 formula alone. The data shows a higher retention of all compounds - most noticeably mid and low volatility notes on the right - even after the high volatility notes on the left has evaporated by 6 hours.
  • the present invention provides compositions that prolong the performance of a fragrance oil.
  • a "long-lasting fragrance composition” as used herein means that a fragrance oil according to the present invention has prolonged performance relative to the fragrance oil alone. Prolonged performance may be measured by methods known in the art. For example, by quantitative GC-MS analysis following evaporation kinetics ; by sensory panels rating over all intensity or rating olfactive attributes.
  • the present invention provides compositions that improve fragrance performance by imparting consumer-perceived long-lasting perception of a perfume during fragrance wear while maintaining a clear, transparent, sprayable and stable hydro-alcoholic formulation and solution with an acceptable skin feel.
  • a long-lasting fragrance composition of the present invention is suitable for volatile solvent (ethanol, for examplej-containing consumer fragrance products for the skin or hair.
  • a long-lasting fragrance composition of the present invention may be dispensed using an atomizer in a micronized mist, which will enhance the fragrance performance thanks to the use of a dispensing system composed of a multichannel nozzle.
  • a long-lasting fragrance composition of the present invention can be diluted by a solvent (e.g., ethanol) - water mixture in order to obtain a final consumer product such as a Cosmetic, Eau de toilette, Eau de perfume, Body-mist, Body spray, Body splash, deodorant , Hair mist, lotion, air care products, and other solvent-based consumer products.
  • a solvent e.g., ethanol
  • the long-lasting fragrance composition can be coupled with non-odoriferous fragrance modulators, odoriferous fragrance modulators, entra ⁇ ment macromolecule like cyclodextrins, and/or profragrances in order to enhance the long-lasting benefits.
  • An amphiphilic oil-soluble compound of the present invention includes a compound having one of the following chemical structures: where n represents the number of CH2 groups and is greater than 14, m represents the number of unsaturated C-C bounds and is greater than or equal to 1, and Ri is one or a combination of the following groups:
  • amphiphilic oil-soluble compound is soluble in the volatile solvent, not soluble or slightly soluble in water, and has a packing parameter > 1.
  • amphiphilic oil-soluble compound is glycerol monooleate, phytantriol, a long chain fatty acid ( CH 2 greater than 14), or a surfactant with a hydrophilic- lipid balance (HLB) less than 10.
  • An amphiphilic oil-soluble compound may be a surface active compound such as a surfactant having a HLB ⁇ 10, long-chained fatty acids and fatty alcohols having CH2>14 such as myristyl, palmityl, oleyl, docosanoyl, and others.
  • a surfactant having a HLB ⁇ 10 long-chained fatty acids and fatty alcohols having CH2>14 such as myristyl, palmityl, oleyl, docosanoyl, and others.
  • a “fragrance oil” according to the present invention includes fragrance, fragrance ingredients, essential oils, and a mix of aroma compounds and natural ingredients such as essential oils, extracts, and resins.
  • the fragrance oil may be 0.01% to 80% w/w of the long-lasting fragrance composition. In an aspect of the invention, the fragrance oil may be 1% to 30% w/w of the long-lasting fragrance composition.
  • a gelator (gelling agent) according to the present invention may be a molecule from the class of Low Molecular Weight Gelators (LMWG) compounds such as long chain (> 16CH2) n-alkanes, hydroxyalkanoic acids as hydroxy-octadecanoyl, hydroxy-hexadecanoyl, etc., dihydroxyalkanoic acids, dicarboxylic acids, fatty acids alkyl ester with alkyl chain length > 20 CH2 groups, hydroxyalkanoic alcohols, steroid derivatives such as glycyrrhizic acid, caffeine, anthryl derivatives, molecules containing steroidal and condensed aromatic rings, dendrimers n-alkanes, oligo(p-phenylenevinylene), dipyridylurea-carboxylic acid combination, diamine linked Dendron, amino acid-based gelators such as dibutyl ethylhexanoyl glutamide and dibutyl lauroyl monogly
  • a volatile solvent according to the present invention has an evaporation rate or vapor pressure higher than that of water.
  • the vapor pressure of water at 35°C is 5.62 kPa.
  • the volatile solvent is ethanol.
  • a long-lasting fragrance of the present invention may include a hydrotrope or hydrotropic salt (e.g., sodium salicylate). Suitable ranges of a hydrotrope or hydrotropic salt are 0 to 5% w/w of the long-lasting fragrance, or 0.01% to 2% w/w of the long-lasting fragrance.
  • a hydrotrope or hydrotropic salt e.g., sodium salicylate.
  • a long-lasting fragrance composition of the present invention may include an osmolyte.
  • An osmolyte may be a slightly water soluble compound such as a humectant( e.g., glycols such as dipropylene glycol, butylene glycol, propylene glycol, glycerine, pentanediols, hexanediols, propanediols, butanediols, xylitol), an emollient, a natural osmolyte (ectoine),and a biopolymer.
  • the osmolyte may be 0 to 1% or 0.01% to 0.5% w/w of the long-lasting fragrance.
  • Leave-on volatile solvent containing consumer products such as perfume, Eau de Toilette, Eau deparfum, Body mist, body spray, Body splash, Hair mist, air care spray, Hair Leave-onproducts, Fabric refreshers, Deodorant, etc.
  • the leave-on volatile solvent containing consumer product may further include a dye, a UV filters, an antioxidant, a quencher, a chelating agent, a solubilizer, a moisturizer, a humectant, an anti-aging active, a soothing agent, an anti-pollution active, emollient or a combination thereof.
  • Eau De Toilette (EDT) formulation was prepared and used as a reference to evaluate fragrance performance. Water was added to ethanol as set forth in Table 1. After stirring, fragrance was added to this solution. The final mixture was stirred until homogeneous.
  • amphiphilic oil-soluble compound phytantriol was dissolved in ethanol. Water was added to this solution. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 2.
  • Example 4 Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice); origin: Sigma-Aldrich.
  • Example 4 EDT containing Phytantriol and Caffeine (EDT3) a) Formulation and Process Phytantriol and caffeine were mixed in ethanol. To this solution was added water. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 4. 1) Ethanol Absolute anhydrous; origin: Carlo Erba.
  • Glycerol monooleate GMO was mixed in ethanol. To this solution was added water. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 6.
  • Isocetyl alcohol (ICA) was mixed in ethanol. To this solution was added water. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 7. 1) Ethanol Absolute anhydrous; origin: Carlo Erba.
  • Example 8 EDT containing glycerol monooleate and isocetyl alcohol Glycerol monooleate (GMO) and isocetyl alcohol (ICA) were mixed in Ethanol. To this solution was added water. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 8. 1) Ethanol Absolute anhydrous; origin: Carlo Erba.
  • Example 9 EDT containing glycerol monooleate, nerolidol and dibutyl ethylhexanoyl glutamide
  • Glycerol monooleate (GMO), nerolidol and dibutyl ethylhexanoyl glutamide (EB-21) were mixed in ethanol. To this solution was added water. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 9.
  • Example 10 EDT containing glycerol monooleate, nerolidol, polymethylol and dibutyl ethylhexanoyl glutamide
  • Glycerol monooleate (GMO) nerolidol, polymethylol and dibutyl ethylhexanoyl glutamide (EB-21) were mixed in ethanol. To this solution was added water. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 10.
  • Example 11 EDT containing glycerol monooleate, nerolidol, polymethylol and dibutyl ethylhexanoyl glutamide
  • Glycerol monooleate (GMO), polymethylol and dibutyl ethylhexanoyl glutamide (EB- 21) were mixed in Ethanol. To this solution was added water. After stirring, fragrance was added to this mixture. The final solution was stirred until homogeneous. See Table 11.
  • Example 12 Performance a) Process Evaporation kinetic studies were performed. The test and reference compositions were deposited on the glass bottom of head-space vials and were evaporated after 2, 4, 6 or sometimes 24 hours at 32°C (corresponding to the skin temperature) under agitation. At a given moment, the vials were closed and left for saturation of the head-space at 32°C. Small amounts of the saturated head-space vapors were injected in GC-MS instrument and the vapor composition was analyzed.
  • a CTC PAL was installed on the GC-MS (6890 series GC system & 5973 network MS) for sample injection.
  • This CTC PAL was equipped with a 1 mL syringe. 1 mL of headspace gas was taken from the samples and injected into a GC-MS instrument. Before each injection, samples were agitated at 32°C for 30 min by the composer of the GCMS.
  • An Agilent GC was used with a split/splitless inlet and Helium as carrier gas.
  • a septum BTO was installed (Bleed & Temp Optimized septa, 11mm / Agilent 5183 - 4757) and the liner was heated at 250°C (liner, splitless, single traper, deactivated / Agilent 5181- 3316). The samples were analyzed with a split ratio 5:1.
  • a non-polar column was mounted in the oven.
  • the analyses were done at constant flow with an initial flow at 1 mL/min (corresponding to an average velocity of 36 cm/s).
  • the oven program started at 40°C. The temperature rose to 150°C with a temperature ramp of 20°C/min, and then rose to 250°C with a temperature ramp of 50°C/min. The oven held the temperature at 250°C for one minute.
  • the perfumery ingredient Styrallyl acetate (provided by Firmenich SA and having a volatility equal to 1320.4 ⁇ g/L air) was solubilized in formulation EdT1-4 and deposited according to "Sample preparation" above. Performance at different times during the evaporation process is shown in Figure 1 as value relative to the intensity of the reference EdT formulation. The results demonstrate increased fragrance performance from formulations EDT1 to 4 after 2 and, even greater, after 4 hours of evaporation compared to the reference sample (EDTO) corresponding to 1.
  • EDTO reference sample
  • Test 1 Model fragrance A, shown in Table 12, was solubilized in EDT2 and deposited as explained in "Sample preparation”. The intensity of the perfumery ingredients, was followed at different times during the evaporation process. The performance of the perfumery ingredients 6 hours after the deposition is shown in Figure 2 as value relative to the intensity of the reference EdT formulation. The values > 1 mean that the intensity was greater than the reference EdTO.
  • Research Accord HT1 used in this experiment consists of below 44 ingredients ranging from high volatility to low volatility ingredients at equal concentrations.
  • Technology 1 Technology 2:
  • 3-Alternative Forced Choice (or 3-AFC) test was used. For each time point, panelists were presented with 3 samples, two of which were the fragrance (SP), and one in which the fragrance was in accordance with the present invention. Panelists indicated the sample(s) that were higher in terms of overall intensity.
  • SP fragrance
  • SP fragrance
  • the fragrance SP contained 44% of fragrance ingredients with log P ⁇ 4 (high volatility).
  • Table 15 shows the higher performance of the formulation according to the present invention after 4 hours of evaporation in the presence of 10% phytantriol, and after 2 hours of evaporation in the presence of 10% GMO.
  • a volatility component in an amount from 35% to 100 wt% of the fragrance component comprising at least one perfume raw material having a first vapor pressure greater than 0.0008 Torr at 22°C; ⁇ And, within the perfume constructions above: o Construction 1 - A volatility component from 40 to 100 wt% of the fragrance component comprising at least one perfume raw material having a first vapor pressure greater than 0.08 torr and optionally, a second at least one perfume raw material having a first vapor pressure greater than 0.08 Torr at 22°C; o Construction 2 - A volatility component in an amount from 0.08 to 85 wt% of the fragrance component, comprising a first at least one perfume raw material having a first vapor pressure range of 0.0008 to 0.08 Torr at 22°C; and, optionally, a second at least one perfume raw material having a first vapor pressure range of 0.0008 to 0.08 Torr at 22°C; c) Conclusion
  • fragrance retention is significant in the EdT formulations containing amphiphilic oil-soluble compounds of the present invention (phytantriol) and low molecular weight gelators.
  • the long-lasting performance of the invention against the standard EdT formulation was confirmed 4-6h after the deposition. Synergistic mixtures were discovered surprisingly providing better fragrance retention.

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Abstract

La présente invention concerne des compositions parfumées à longue durée de vie qui confèrent à un consommateur une perception et/ou une intensité durables d'un parfum pendant le port du parfum. La présente invention fournit des compositions de parfum de longue durée pour prolonger la performance d'une huile parfumée.
EP21710183.1A 2020-02-04 2021-02-02 Formulations offrant une performance parfumée de longue durée Pending EP4076362A1 (fr)

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EP0616800A3 (fr) * 1993-03-22 1995-02-15 Givaudan Roure Int Composition odorante avec diffusion prologée.
BR0213446A (pt) * 2001-10-24 2004-11-09 Dsm Ip Assets Bv Uso de um protetor solar de polissiloxano para acentuar retenção de fragrância no cabelo
KR101142008B1 (ko) * 2009-06-11 2012-05-17 주식회사 코리아나화장품 천녀목란 줄기세포 배양산물을 유효성분으로 함유하는 화장료 조성물
PL2579839T3 (pl) * 2010-06-10 2016-07-29 Firmenich & Cie Kompozycje perfumeryjne i ich zastosowania
US9428712B2 (en) * 2011-11-04 2016-08-30 Firmenich Sa Perfuming compositions and uses thereof
ES2664070T3 (es) * 2012-12-13 2018-04-18 Firmenich Sa Composiciones perfumantes en microemulsión sin etanol
JP6920209B2 (ja) * 2015-04-09 2021-08-18 モメンティブ パフォーマンス マテリアルズ インコーポレイテッドＭｏｍｅｎｔｉｖｅ Ｐｅｒｆｏｒｍａｎｃｅ Ｍａｔｅｒｉａｌｓ Ｉｎｃ． 長期持続性芳香放出組成物
EP3103431A1 (fr) * 2015-06-12 2016-12-14 The Procter and Gamble Company Compositions de parfums et utilisations associées
EP3103523A1 (fr) * 2015-06-12 2016-12-14 The Procter and Gamble Company Article absorbant comprenant une composition de parfum
WO2017017251A1 (fr) * 2015-07-29 2017-02-02 Firmenich Sa Gel purificateur d'air contenant de la cellulose, de l'hémicellulose, de la lignine
EP4331684A3 (fr) * 2017-08-09 2024-05-29 Symrise AG 1,2-alcanediols
CN108888553A (zh) * 2018-07-24 2018-11-27 上海韵宜生物科技有限公司 一种香氛喷雾及其制备方法

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BR112022015029A2 (pt) 2022-09-20

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